Hydrophilic film

Patent metadata

Field	Value
Publication number	US-9512034-B2
Application number	US-93374309-A
Country	US
Kind code	B2
Filing date	Mar 19, 2009
Priority date	Mar 21, 2008
Publication date	Dec 6, 2016
Grant date	Dec 6, 2016

Abstract

A hydrophilic film that has high adhesion to inorganic materials and is safer and excellent in transparency and also exhibits both very high hydrophilicity and abrasion resistance, and a laminate including the hydrophilic film. The hydrophilic film is produced by applying a specific hydrophilic compound (c) having an acryloyl group and a potassium sulfonate group or the like to a surface of a layer formed from a mixture containing a silane compound (a) including one silicon atom, a mercapto group or the like, and at least one silicon-bonded group, and a silane compound (b) including at least four silicon-bonded groups and not including groups reactive with a carbon-carbon double bond, and allowing a reaction between at least a part of acryloyl groups contained in the hydrophilic compound (c) and at least a part of mercapto groups derived from the compound (a).

First claim

The invention claimed is:

1. A laminate comprising a hydrophilic film, a hardened material layer and an inorganic base material obtained by a process comprising steps of:
(A) preparing a mixture containing:
a silane compound (a) including one silicon atom, a group selected from the group consisting of a mercapto group and an amino group, and at least one silicon-bonded group selected from the group consisting of an alkoxy group, a halogen group, and a hydroxyl group, and
a silane compound (b) including a cross-linkable silicon-bonded group selected from the group consisting of an alkoxy group, a halogen group, and a hydroxyl group, the silane compound (b) not including groups reactive with a carbon-carbon double bond;
(B) applying the mixture to the inorganic base material to form a hardened material layer on the inorganic base material by a condensation reaction of the mixture;
(C) applying a solution containing a hydrophilic compound represented by following general formula (c) dissolved in a solvent to a surface of the hardened material layer; and
(D) forming the hydrophilic film by allowing a direct reaction between at least a part of (meth)acryloyl groups contained in the hydrophilic compound represented by the general formula (c) and at least a part of groups derived from the silane compound (a), being selected from the group consisting of a mercapto group and an amino group by means of heat or radiation rays,

wherein in the formula (c), R represents H or CH 3 ; R 3 to R 8 independently represent H, CH 3 , or OH, represents an integer 0 to 18; n represents an integer of 1 to 10; q represents 1 or 2; and M represents H, Li, Na, K, Rb, Mg, Ca, Sr, or Ba,
wherein the molar ratio of the silane compound (a)/the silane compound (b) is 1/2 to 1/200.

2. A method of producing a laminate having a hydrophilic film and a hardened material layer on an inorganic base material produced by
(A) preparing a mixture containing:
a silane compound (a) including one silicon atom, a group selected from the group consisting of a mercapto group and an amino group, and at least one silicon-bonded group selected from the group consisting of an alkoxy group, a halogen group, and a hydroxy group, and
a silane compound (b) including a cross-linkable silicon-bonded group selected from the group consisting of an alkoxy group, a halogen group, and a hydroxy group and not including groups reactive with a carbon-carbon double bond, wherein the molar ratio of the silane compound (a)/the silane compound (b) is 1/2 to 1/200;
(B) applying the mixture to the inorganic base material and allowing hydrolysis and condensation reactions to progress and form the hardened material layer on a surface of the inorganic base material;
(C) applying a solution containing a hydrophilic compound represented by the following general formula (c) dissolved in a solvent to a surface of the hardened material layer; and
(D) forming the hydrophilic film by allowing a grafting reaction directly between at least a part of (meth)acryloyl groups contained in the hydrophilic compound represented by the general formula (c) and at least a part of groups derived from the silane compound (a), being selected from the group consisting of a mercapto group and an amino group by means of heat or radiation rays to progress and form the hydrophilic film,

wherein in the formula (c), R represents H or CH 3 ; R 3 to R 8 independently represent H, CH 3 , or OH; m represents an integer of 0 to 18; n represents an integer of 1 to 10; q represents 1 or 2; and M represents H, Li, Na, K, Rb, Mg, Ca, Sr, or Ba.

3. The method of producing a laminate having a hydrophilic film according to claim 2 , wherein M of the compound (c) is H, Li, Na, Rb, Mg, Ca, Sr, or Ba; and the grafting reaction is performed under a temperature condition of 130° C. or higher.

4. The laminate according to claim 1 , wherein the molar ratio of the silane compound (a)/the silane compound (b) is 1/3 to 1/100.

5. The laminate according to claim 1 , wherein the molar ratio of the silane compound (a)/the silane compound (b) is 1/4 to 1/100.

6. The laminate according to claim 1 , wherein the molar ratio of the silane compound (a)/the silane compound (b) is 1/3 to 1/50.

7. The laminate according to claim 1 , wherein the molar ratio of the silane compound (a)/the silane compound (b) is 1/4 to 1/30.

8. The laminate according to claim 1 , wherein the silane compound (a) has the one silicon atom, the mercapto or amino group, and the alkoxy group as the at least one silicon-bonded group, or wherein the silane compound (b) has the alkoxy group as the cross-linkable silicon-bonded group.

9. The laminate according to claim 1 , wherein in the formula (c), R 3 to R 8 each represent H; m represents an integer of 0 to 8; n represents an integer of 1 to 3; and M represents H, Li, Na, K or Ca.

10. The method according to claim 2 , wherein the molar ratio of the silane compound (a)/the silane compound (b) is 1/3 to 1/100.

11. The method according to claim 2 , wherein the molar ratio of the silane compound (a)/the silane compound (b) is 1/4 to 1/100.

12. The method according to claim 2 , wherein the molar ratio of the silane compound (a)/the silane compound (b) is 1/3 to 1/50.

13. The method according to claim 2 , wherein the molar ratio of the silane compound (a)/the silane compound (b) is 1/4 to 1/30.

14. The method according to claim 2 , wherein the silane compound (a) has the one silicon atom, the mercapto or amino group, and the alkoxy group as the at least one silicon-bonded group, or wherein the silane compound (b) has the alkoxy group as the cross-linkable silicon-bonded group.

15. The method according to claim 2 , wherein in the formula (c), R 3 to R 8 each represent H; m represents an integer of 0 to 8; n represents an integer of 1 to 3; and M represents H, Li, Na, K or Ca.

Assignees

• Okazaki Koju
• Kawasaki Noboru
• Mitsui Chemicals Inc

Inventors

• Okazaki Koju
• Kawasaki Noboru

Classifications

• C09D4/06

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00 · CPC title

• C03C2217/75

  Hydrophilic and oleophilic coatings · CPC title

• C08G77/28

  sulfur-containing groups · CPC title

• C09D183/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• Y10T428/31663

  As siloxane, silicone or silane · CPC title